Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides

被引：114

作者：

Abraham, Ciby J. ^{[1
]}

Paull, Daniel H. ^{[1
]}

Scerba, Michael T. ^{[1
]}

Grebinski, James W. ^{[1
]}

Lectka, Thomas ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 41期

关键词：

D O I：

10.1021/ja065754d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this Communication, we report a system in which an achiral Lewis acid (activating the diene) works in concert with a chiral nucleophile (dienophile) to effect the first highly enantio- and regioselective catalytic inverse electron demand Diels-Alder [4 + 2] cycloaddition reaction to form biologically active quinoxalinones from ketene enolates and o-benzoquinone diimides in good to excellent yields with >99% ee. Copyright © 2006 American Chemical Society.

引用

页码：13370 / 13371

页数：2

共 22 条

[1] QUINONE IMIDES .25. ORTHO-QUINONEDIBENZIMIDES [J].

ADAMS, R ;

WAY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (10) :2763-2769

[2]

[Anonymous], 1989, PROG HET CH

[3] Catalytic, enantioselective [4+2]-cycloadditions of ketene enolates and o-quinones:: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives [J].

Bekele, T ;

Shah, MH ;

Wolfer, J ;

Abraham, CJ ;

Weatherwax, A ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1810-1811

[4] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES [J].

BUNIN, BA ;

ELLMAN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10997-10998

[5] Recent advances in homogeneous enantioselective Diels-Alder reactions catalyzed by chiral transition-metal complexes [J].

Carmona, D ;

Lamata, MP ;

Oro, LA .

COORDINATION CHEMISTRY REVIEWS, 2000, 200 :717-772

[6] Synthesis, characterization, and metal complexes of a salen ligand containing a quinoline base [J].

DiMauro, EF ;

Mamai, A ;

Kozlowski, MC .

ORGANOMETALLICS, 2003, 22 (04) :850-855

[7] Bifunctional lewis acid-nucleophile-based asymmetric catalysis:: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams [J].

France, S ;

Shah, MH ;

Weatherwax, A ;

Wack, H ;

Roth, JP ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1206-1215

[8] Synthesis and pharmacological evaluation of substituted 5-[4-[2-(6,7-dimethyl-1,2,3,4-tetrahydro-2-oxo-4-quinoxalinyl)ethoxylphenyllmethylenelthiazolidine-2,4-dione derivatives as potent euglycemic and hypolipidemic agents [J].

Gupta, D ;

Ghosh, NN ;

Chandra, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (04) :1019-1022

[9] The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].

Horton, DA ;

Bourne, GT ;

Smythe, ML .

CHEMICAL REVIEWS, 2003, 103 (03) :893-930

[10] SYNTHESIS AND SOME PROPERTIES OF 1H-1-BENZAZEPINES [J].

IKEDA, M ;

OHNO, K ;

UNO, T ;

TAMURA, Y .

TETRAHEDRON LETTERS, 1980, 21 (35) :3403-3406

← 1 2 3 →